Triethylsilane → HCID 69386020, compound

HRID 860973Notes

Reaction equation

HRID 860973 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[C:16]([Br:18])[C:15]([O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[C:23]([OH:29])=[C:22]([CH:30]=O)[CH:21]=2)=[C:14]([Br:32])[CH:13]=1>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[C:16]([Br:18])[C:15]([O:19][C:20]2[CH:21]=[C:22]([CH3:30])[C:23]([OH:29])=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:25]=2)=[C:14]([Br:32])[CH:13]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 87807692HCID 87807692, compound

Product 1

HCID 69386020HCID 69386020, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane was added to a mixture of methyl[3,5-dibromo-4-(3-formyl-4-hydroxy-5-isopropylphenoxy)phenyl]acetate (243 mg, 0.5 mmol) and trifluoroacetic acid (10 mL) at room temperature. After 12 hours stirring, the reaction mixture was concentrated via co-evaporated with toluene. The residue was purified on column (silica, gradient elution: n-heptane/ethyl acetate from 9:1 to 7:3) to give 197 mg (84%) of methyl[3,5-dibromo-4-(4-hydroxy-3-isopropyl-5-methylphenoxy)phenyl]acetate.

Workup

  1. concentrationthe reaction mixture was concentrated via co-evaporated with toluene
  2. customThe residue was purified on column (silica, gradient elution: n-heptane/ethyl acetate from 9:1 to 7:3)

Sources & evidence

ORD record
ord-cffed95b2ef24e4288a82b7c6ab957c1
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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